CN102675269B - 苯并呋喃衍生物及其应用 - Google Patents
苯并呋喃衍生物及其应用 Download PDFInfo
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- CN102675269B CN102675269B CN201110142267.0A CN201110142267A CN102675269B CN 102675269 B CN102675269 B CN 102675269B CN 201110142267 A CN201110142267 A CN 201110142267A CN 102675269 B CN102675269 B CN 102675269B
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- Prior art keywords
- hydrogen
- alkyl
- compound
- tributyl
- antioxidant
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- 150000001907 coumarones Chemical class 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 38
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 18
- 239000011368 organic material Substances 0.000 claims description 18
- 230000003064 anti-oxidating effect Effects 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000004033 plastic Substances 0.000 abstract description 14
- 229920003023 plastic Polymers 0.000 abstract description 14
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 description 35
- 150000003254 radicals Chemical class 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- -1 compound free radical Chemical class 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 3
- 229960001545 hydrotalcite Drugs 0.000 description 3
- 229910001701 hydrotalcite Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 150000003014 phosphoric acid esters Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- NBDBHSGFKCVICR-UHFFFAOYSA-N 4-hydroxy-3-phenyl-3h-1-benzofuran-2-one Chemical class C1=2C(O)=CC=CC=2OC(=O)C1C1=CC=CC=C1 NBDBHSGFKCVICR-UHFFFAOYSA-N 0.000 description 1
- CYHYIIFODCKQNP-UHFFFAOYSA-N 5,7-ditert-butyl-3-(3,4-dimethylphenyl)-3h-1-benzofuran-2-one Chemical compound C1=C(C)C(C)=CC=C1C1C(C=C(C=C2C(C)(C)C)C(C)(C)C)=C2OC1=O CYHYIIFODCKQNP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- RWKRHVUWAYFXKF-UHFFFAOYSA-N CC(C)(C)c(cc1C2c(cc(C(C)(C)C)cc3)c3OC(c3ccccc3)=C)ccc1OC2=O Chemical compound CC(C)(C)c(cc1C2c(cc(C(C)(C)C)cc3)c3OC(c3ccccc3)=C)ccc1OC2=O RWKRHVUWAYFXKF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000000937 inactivator Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Furan Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW100109042 | 2011-03-17 | ||
| TW100109042A TWI403507B (zh) | 2011-03-17 | 2011-03-17 | 苯并呋喃衍生物及其應用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102675269A CN102675269A (zh) | 2012-09-19 |
| CN102675269B true CN102675269B (zh) | 2014-06-25 |
Family
ID=44905373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110142267.0A Active CN102675269B (zh) | 2011-03-17 | 2011-05-30 | 苯并呋喃衍生物及其应用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8840810B2 (ja) |
| EP (1) | EP2500341B1 (ja) |
| JP (1) | JP5280501B2 (ja) |
| KR (1) | KR101338786B1 (ja) |
| CN (1) | CN102675269B (ja) |
| ES (1) | ES2426979T3 (ja) |
| TW (1) | TWI403507B (ja) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015044785A2 (en) | 2013-09-27 | 2015-04-02 | Basf Se | Polyolefin compositions for building materials |
| TWI685524B (zh) | 2013-12-17 | 2020-02-21 | 美商畢克美國股份有限公司 | 預先脫層之層狀材料 |
| PL3107959T3 (pl) * | 2014-02-17 | 2019-01-31 | Basf Se | Pochodne 3-fenylobenzofuran-2-onu zawierające fosfor jako stabilizatory |
| PL3177681T3 (pl) * | 2014-08-05 | 2019-02-28 | Basf Se | Pochodne difosforynu 3-fenylobenzofuran-2-onu jako stabilizatory |
| DK3067343T3 (en) | 2015-03-10 | 2018-11-19 | Evonik Degussa Gmbh | Antioxidants for the production of low emission pur systems |
| JP6771538B2 (ja) | 2015-07-20 | 2020-10-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 難燃性ポリオレフィン物品 |
| WO2017025431A1 (en) * | 2015-08-10 | 2017-02-16 | Basf Se | 3-phenyl-benzofuran-2-one derivatives containing phosphorus as stabilizers |
| JP2020526609A (ja) | 2017-07-06 | 2020-08-31 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ベンゾフラノンおよびヒンダードフェノール系酸化防止剤を含む安定化ポリオレフィン組成物 |
| BR112020009154A2 (pt) * | 2017-11-14 | 2020-10-27 | Basf Se | composição filme, folha ou artigo moldado, métodos para preparar o filme, folha ou artigo moldado e para estabilizar policarbonato contra os efeitos deletérios do calor, luz e oxigênio, e, composição aditiva |
| EP3810621A1 (en) | 2018-06-21 | 2021-04-28 | Basf Se | 3-phenyl-benzofuran-2-one diphosphate derivatives as stabilizers |
| PL3841166T3 (pl) | 2018-08-22 | 2022-09-26 | Basf Se | Stabilizowana poliolefina formowana rotacyjnie |
| US20220282064A1 (en) | 2019-07-30 | 2022-09-08 | Basf Se | Stabilizer composition |
| CN111117216B (zh) * | 2019-12-19 | 2021-09-17 | 金发科技股份有限公司 | 一种聚酰胺组合物及其制备方法 |
| CA3230749A1 (en) | 2021-09-02 | 2023-03-09 | Cinzia Tartarini | Stabilizer combination for preventing degradation of synthetic polymers |
| WO2023202971A1 (en) | 2022-04-20 | 2023-10-26 | Basf Se | An aqueous antioxidant suspoemulsion and a process for preparing the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4325863A (en) * | 1979-02-05 | 1982-04-20 | Sandoz Ltd. | Benzofuranone or indolinone compounds useful as stabilizers for organic materials |
| CN1407005A (zh) * | 2001-09-11 | 2003-04-02 | 西巴特殊化学品控股有限公司 | 合成聚合物的稳定方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1982432A (en) * | 1933-06-10 | 1934-11-27 | Rubert A Hull | Cemetery monument |
| MX9305489A (es) * | 1992-09-23 | 1994-03-31 | Ciba Geigy Ag | 3-(dihidrobenzofuran-5-il)benzofuran-2-onas, estabilizadores. |
| TW284762B (ja) | 1993-09-17 | 1996-09-01 | Ciba Geigy Ag | |
| DE19714614A1 (de) * | 1997-04-09 | 1998-10-15 | Agfa Gevaert Ag | Farbfotografisches Silberhalogenidmaterial |
| DE10153698A1 (de) * | 2001-10-31 | 2003-05-15 | Agfa Gevaert Ag | Fotografisches Silberhalogenidmaterial |
| JP2009057453A (ja) * | 2007-08-31 | 2009-03-19 | Konica Minolta Opto Inc | 溶融流延用セルロースアシレート製剤、セルロースアシレートフィルムの製造方法、セルロースアシレートフィルム及び延伸セルロースアシレートフィルム |
| JP2012520365A (ja) * | 2009-03-13 | 2012-09-06 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリエステル及びポリアミドの安定化されたブレンド |
-
2011
- 2011-03-17 TW TW100109042A patent/TWI403507B/zh active
- 2011-05-30 CN CN201110142267.0A patent/CN102675269B/zh active Active
- 2011-08-24 US US13/137,530 patent/US8840810B2/en active Active
- 2011-08-31 JP JP2011189559A patent/JP5280501B2/ja active Active
- 2011-09-06 EP EP11180289.8A patent/EP2500341B1/en active Active
- 2011-09-06 ES ES11180289T patent/ES2426979T3/es active Active
- 2011-10-04 KR KR1020110100603A patent/KR101338786B1/ko active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4325863A (en) * | 1979-02-05 | 1982-04-20 | Sandoz Ltd. | Benzofuranone or indolinone compounds useful as stabilizers for organic materials |
| US4338244A (en) * | 1979-02-05 | 1982-07-06 | Sandoz Ltd. | Benzofuran(2)one or indolin(2)one compounds useful as stabilizers for organic materials |
| CN1407005A (zh) * | 2001-09-11 | 2003-04-02 | 西巴特殊化学品控股有限公司 | 合成聚合物的稳定方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012193158A (ja) | 2012-10-11 |
| JP5280501B2 (ja) | 2013-09-04 |
| TWI403507B (zh) | 2013-08-01 |
| KR20120106532A (ko) | 2012-09-26 |
| CN102675269A (zh) | 2012-09-19 |
| KR101338786B1 (ko) | 2013-12-06 |
| US20120238677A1 (en) | 2012-09-20 |
| US8840810B2 (en) | 2014-09-23 |
| ES2426979T3 (es) | 2013-10-28 |
| TW201238957A (en) | 2012-10-01 |
| EP2500341B1 (en) | 2013-06-26 |
| EP2500341A1 (en) | 2012-09-19 |
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